Should I sleep with a married man?

Dear Pleasure Principal,

I am contemplating sleeping with a married guy. I’ve known him for about a year-and-a-half, but only because we’re part of the same networking group, and he is super attractive. What is really attractive about him is that other people—men and women—find him really attractive, and he’s really into me. He has sort of an open relationship with his wife—she just doesn’t want to know. What would be the harm?

Hi Contemplater,

I want to dissect your question and really dig in there and ask you a lot of questions that you can then ask yourself. 

Ethical Non-Monogamy

"He has sort of an open relationship with his wife..."

First off, if you are interested in sex only and you want to go ahead with sleeping with this guy, and you believe his wife is cool with it (which I think matters to you because you mention it), then why are you asking me this question? Could it be that you want permission to do it because you want to do it, but something about it bothers you? Getting “permission” from anyone externalizes the justification for behavior that you know may be ethically grey and morally wrong and perhaps, psychologically, reduces your responsibility if or when it all goes sideways and you have an angry or crushed wife calling your cell phone at 1:00 in the morning to see if her husband is there with you. 

Second, Couples involved in ENM or polyamory are not typically "sort of" open to other sexual play partners. It is openly discussed and affirmed or massaged until the terms can be re-negotiated. For this guy and his wife, it may be openly discussed, but if he is saying it is "sort of" open, then it sounds to me like he has broached the topic, and she has reluctantly agreed but it is painful on some level to her. That, in my book, means it is NOT, in fact, open. It also means that while he would probably really like to have sex with you, you need to fully accept that his dance card is full with a wife and a life and probably some kids and a mortgage and a job, and sexual novelty is a good way for him to blow off steam. The only way to really know is to have truly open communication (with him, for sure, but maybe also his wife, but only if he introduced you) and to monitor for non- or half-truths that are self-serving on everyone's part.

Psychological Motivators

“…he is super attractive. What is really attractive about him is that other people—men and women—find him really attractive, and he’s really into me.”

There is something about his attraction to you that sounds like it might feed your ego, and that is an ego that could stem from an insecure place. When we base attraction on things like physical and cultural surface values—envy, lust, immediate gratification—we are likely in it for unconscious reasons that may not actually serve our bigger goals. However, study after study shows that women select for sex partners with more masculine physical traits (strong jaw, deeper voice, facial hair, wider shoulders than hips) during ovulation and luteal phases of the menstrual cycle*. And if your reason is simply sex, then I do want to challenge you to look at whether that is honestly and deeply true for you. If it is, happy hunting. If it is not, then there is more to look at in terms of why you want to be a woman hunting simply for sex. Is it because you hope that he will fall in love with you once he has had the sex with you? It could happen, but that’s a rarity.

Questions for you to reflect on: 

What validation might you need that you are missing and do not, cannot, or won’t give to yourself? Is it a lifelong pattern where you seek justification and validation from external sources? 

The Ethos Question

I am not big into religious morality, but there are things that fall generally into ethics and morals because we understand that some behaviors and conduct fall into institutionally “right” and “wrong” and personally “right” and “wrong”. While they are sometimes used interchangeably, they are different: ethics refer to rules provided by an external source (such as workplace codes of conduct or principles in religions) and morals refer to an individual's own principles regarding right and wrong and are often dictated rules by an institution that are downloaded and integrated like an internal program. Both ethics and morals are based on systems of principles that govern subjective ideals of “a good life” and really work best when there is some personal analysis and judicious reasoning that goes along with them. Personal morals come down to the influence of the broad social ethical culture (national, ethnic, judicial, economic, popular entertainment), what you were taught in your upbringing (influence of family, church, school, etc.), and your personal values (your own principles, beliefs, and ideals).

Questions for you to reflect on: 

Who do you believe yourself to be, in terms of how you think a “good” person behaves? Does sleeping with a married man “just for sex” fall into your category of a “good life” or a life well-lived or how a “good” or "bad" person behaves in the world?  How are you qualifying and quantifying yourself, the guy, or the sex in general, and how do you qualify it with a guy who says he is "sort of" in an open relationship?

The answers to all of these questions provide you with good insight into yourself. Before you sleep with anyone, it is best to have a pulse on your own self, what you like, what makes you tick, what you believe in. Finding a mate or a sex partner becomes much easier when you have that strong sense of self, a strong grasp of your inner compass. It makes it easier to read others and have an idea right out of the gate on where in your friend or lover group the new person will reside in your heart and social spheres.

* Not ALL studies support this, and there is some disagreement on this in the field.

How do you know when you're ready to have sex?

This week’s column is from an anonymous question box at an American high school. All questions were submitted by students. If your school would like to install an anonymous question box for sexual health to be answered by The Pleasure Principal, please send an email.

Dear Pleasure Principal,

How do you know when you’re ready to have sex?

Dear Anonymous,

There are three things I think every person who is thinking about having sex ought to consider: Truthful Communication, Boundaries, and Trust. Anyone who is thinking about inviting someone else into their sexual space would do well to understand their own bodies, their own boundaries, and be able to communicate their hopes, desires, and edges, and be able to communicate these with someone who has their trust. If you do not trust a person with whom you are considering having some kind of sexual liaison with, or cannot express your desires, fear, or boundaries, then it is a fair assumption that this is probably not the right time or the right person to have the sex with. 

One thing that always gets me about this question is the presumption that “sex” means penetrative intercourse with another person. Kissing and petting is sexual expression. So is oral sex and anal sex. There are many young people I’ve talked to who have stated they are not having sex, meaning vaginal-penis penetrative sex, when they are having fully penetrative anal sex. Anal sex is sex. Fingering is sex. Oral sex is sex. Masturbation is sex. Mutual masturbation is sex, and some call it the safest sex you can have, which is silly because Sex for One is the safest sex you can have.

I am a huge fan of pleasure for one. It allows you to become comfortable in your own body, get intimate with your skin and erogenous zones outside of your genitalia, and allows you to map your likes, desires, timing, and rhythms that you could then give voice to with a partner. When you know how to get yourself off, it is far easier to go into sex with someone else with a better idea of who you are as a sexual being, and can give you more confidence about moving your partner’s hand, tongue, nose, penis, breast, vagina, or feather to the exact spot on your body that calls to be touched, and/or use your words to direct same said action.

What is a dental dam? How do you use it?

This week’s column is from an anonymous question box at an American high school. All questions were submitted by students. If your school would like to install an anonymous question box for sexual health to be answered by The Pleasure Principal, please send an email.

Dear Pleasure Principal,

What is a dental dam and how do you use it?

Dear Anonymous,

A dental dam is a waterproof piece of latex or silicone that is laid flat on the genitals of the person you are about to have oral sex with. It is a barrier device to limit exposure to STIs--both given and received. It is most commonly used on females (cunnilingus), but it is also used on the anus of anyone of any sex for oral-to-anus stimulation (anilingus). 

Ready-to-use dental dams can be purchased online, but you can also easily make one from a condom. [See below, "Make Your Own"]

How To Use a Dental Dam

  1. Carefully open dental dam and remove from package.
  2. Place dental dam flat to cover vaginal opening or anus.
  3. Throw away used dental dam in trash.

Usage: One Time ONLY 

During oral-vaginal sex (also called cunnilingus), simply place the dental dam between your mouth and the vagina.

During oral-anal sex or rimming (also called anilingus,) place the dental dam between your mouth and the anus.

Again, you should only use a dental dam one time.

Dental Dam Dos and Don’ts

  • DO use a new latex or polyurethane dental dam every time you have oral sex.
  • DO read the package and check the expiration date.
  • DO make sure there are no tears or defects.
  • DO put on before starting oral sex and keep it on until finished.
  • DO use water-based or silicone-based lubricant to prevent breakage.
  • DO store dental dams in a cool, dry place.

  • DON’T reuse a dental dam.
  • DON’T stretch a dental dam, as this can cause it to tear.
  • DON’T use nonoxynol-9 (a spermicide), which can cause irritation.
  • DON’T use oil-based products like baby oil, lotion, petroleum jelly, or cooking oil because they will cause the dental dam to break.
  • DON’T flush dental dams down the toilet as they may clog it.

How To Make a Dental Dam From a Condom*

If you can't find dental dams at your local store, or if they cost too much, there's good news. You can actually make your own dental dams at home (unlike condoms which should never be made from plastic wrap.) All you need is a condom and scissors: 

  1. Carefully open package, remove condom, and unroll.
  2. Cut off tip of condom.
  3. Cut off bottom of condom.
  4. Cut down one side of condom.
  5. Lay flat to cover vaginal opening or anus.

If you are going to make your own dental dam, it's best to use a non-lubricated latex condom. If the condom is lubricated, make sure that it does not contain spermicide, as this could numb your tongue or taste funny. A flavored condom may actually be your best option, simply because it's supposed to taste good! You can also find a flavored lubricant to use as well. 

*Be sure the condom is made of latex or polyurethane.


There is little research on this thin, flexible piece of latex that protects against direct mouth-to- genital or mouth-to-anus contact during oral sex so there is little information on how effective dental dams are, but  similar to condoms, people must use them properly and consistently for full protection. It is possible to transmit other infections, such as herpes simplex type 1 and 2, human papillomavirus (HPV), and pubic lice (crabs

The Center for Disease Control (CDC) is perhaps our best government department (so we definitely NEVER want to limit funding or research opps) has this to say about Dental Dams:


What is HPV and why is it everywhere?

This week’s column is from an anonymous question box at an American high school. All questions were submitted by students. If your school would like to install an anonymous question box for sexual health to be answered by The Pleasure Principal, please send an email.

Dear Pleasure Principal,

What is a dental dam and how do you use it?

Dear Anonymous,

HPV is Human Papillomavirus, which is the most common sexually transmitted infection (STI). There are over 200 types of HPV, and most resolve on their own (with the help of your strong antibodies to help you ward off infections). If you have a wart on your hands or feet, it is not the same wart family as the HPV that shows up on your genitalia and back of the throat. Only two types of HPV are known to cause genital warts. There are two known types that cause cervical cancer, and this is the biggest reason we see HPV as a public health issue. This is another reason why a three-part vaccine was developed. 

Some HPV infections can lead to cancer

Most HPV infections (9 out of 10) go away by themselves within two years. But, sometimes HPV infections will last longer, and can cause certain types of cancers. HPV infections can cause cancers of the:

  • cervix, vagina, and vulva in women;
  • penis in men; and
  • anus and back of the throat, including the base of the tongue and tonsils (oropharynx), in both women and men.

Every year in the United States, HPV is estimated to cause nearly 35,000 cases of cancer in men and women.

Prevent cancer with the HPV vaccine

CDC recommends all boys and girls get two doses of the HPV vaccine at ages 11 or 12. HPV vaccination can be started at age 9. For the HPV vaccine to be most effective, the series should be given prior to exposure to HPV. HPV vaccine is recommended at ages 11 to 12 to ensure children are protected long before they are ever exposed to the virus.

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Children who get the first dose before their 15th birthday only need two doses. Children who get the first dose on or after their 15th birthday need three doses.

HPV infections are so common that nearly all men and women will get at least one type of HPV at some point in their lives. Nearly 80 million Americans are currently infected with some type of HPV. About 14 million Americans, including teens, become infected each year.

How do you get HPV?

HPV is easily spread from sexual skin-to-skin contact with someone who has it. You get it when your vulva, vagina, cervix, penis, or anus touches someone else’s genitals or mouth and throat — usually during sex. HPV can be spread even if no one cums, and even if a penis doesn’t go inside the vagina/anus/mouth.

It is really important to remember that HPV is really common, and therefore it is important to de-shamify it. If you find that you have HPV (most likely from an abnormal pap), it is also really important to calm yourself before blaming a sexual partner.

It is ALSO really important to remember to practice SAFER SEX. There is no such thing as safe, but we don't have to be idiots, answering our primitive call to mate without using our really large brains, so use dental dams, use condoms, and do this always as a way to love yourself, be respectful of your sexual partner(s), and as a matter of good public health. HPV is the most common STD, but most of the time it isn’t a big deal. It usually goes away on its own, and most people don’t even know that they ever had HPV. Remember that most people who have sex get HPV at some point in their lives. You don’t need to be ashamed or afraid.

Content source:  National Center for HIV/AIDS, Viral Hepatitis, STD, and TB Prevention , National Center for Immunization and Respiratory Diseases , National Center for Chronic Disease Prevention and Health Promotion




Circumcision in adulthood

Dear Pleasure Principal,

I'm 18 and uncircumcised. I think it's weird and I feel different. Should I have an operation to get circumcised now? Do you think women would want to have sex with me if I got circumcised? P.S. I'm a virgin.

Dear Young Man,

First off, thank you for your courage in being so open and direct. As you know, the main difference between a circumcised (cut) and uncircumcised (uncut) penis is the presence of foreskin around the head of the penis. There are a number of things to consider before deciding to have a circumcision as an adult, beginning with learning about the practice of circumcision. 

Circumcision is  is an ancient practice of the surgical removal of the foreskin (the tissue covering the head (glans) of the penis). With its origin in ancient religious rites, it most commonly occurs in the first day or two of a male's life (although it is performed on the eighth day of life in Jewish populations).  

Is circumcision necessary for medical or health reasons?

This is a highly debated question. It is thought that it originated for hygiene reasons--the accumulation of smegma under the foreskin can cause bacterial infections--especially in ancient times when access to water or bathing was not as frequent as now. But that is not the case for the majority of people in the modern world, so why continue the practice? Things like culture, religion, and personal preference is usually involved in parents' decision. The American Academy of Pediatrics (AAP) found, however, that while the health benefits of newborn male circumcision outweigh the risks, the benefits are not great enough to recommend universal newborn circumcision. Older boys and men who were not circumcised or adequately circumcised may be recommended for circumcision to treat phimosis (the inability to retract the foreskin) or to treat an infection of the penis. 

How is circumcision done?

During a circumcision, the foreskin is freed from the head of the penis, and the excess foreskin is clipped off. If done in the newborn period, the procedure takes about five to 10 minutes. Adult circumcision takes about one hour. The circumcision generally heals in five to seven days. 

Potential Benefits of Circumcision

  • A decreased risk of urinary tract infections.
  • A reduced risk of some sexually transmitted diseases in men.
  • Protection against penile cancer and a reduced risk of cervical cancer in female sex partners.
  • Prevention of balanitis (inflammation of the glans) and balanoposthitis (inflammation of the glans and foreskin).
  • Prevention of phimosis (the inability to retract the foreskin) and paraphimosis (the inability to return the foreskin to its original location).
  • Hygiene: Circumcision also makes it easier to keep the end of the penis clean. Note: Some studies show that good hygiene can help prevent certain problems with the penis, including infections and swelling, even if the penis is not circumcised. In addition, using a condomduring sex will help prevent STDs and other infections.

Potential Problems Associated with Circumcision 

  • Pain.
  • Risk of bleeding and infection at the site of the circumcision.
  • Irritation of the glans.
  • Increased risk of meatitis (inflammation of the opening of the penis)
  • Risk of injury to the penis.

One of the things I question about any adult male wanting to have surgery to be circumcised is the mental and emotional state of wanting it. Personal preference may be just that, but what is the preference based in? When we base any of our sexual ideas on the fiction of porn, we are judging ourselves on a false baseline. There is nothing true, real, or enviable about sex in porn. It is, like Hollywood or fashion, based on an impossible premise of outliers in the population. It is both a narcissistic and self-loathing proposition to hate any trait about the self that is based in an aesthetic. 

As to whether I think women will want to have sex with you more after you've had a circumcision, it is important that you realise that most women are attracted to men who are confident, regardless of penis size, shape, or foreskin. That confidence can be found in men of all penis sizes, shapes, and foreskins, and so can a lack of confidence. So if you were confident and attracted a female that wanted to have sex with you today, would your foreskin bother you so much? It is possible that you could become much more confident with a circumcised penis, but it is also possible that the confidence lacked is more from your feelings of worthiness or unworthiness, and that is not going to be healed by a circumcision. This is the type of self-reflection and introspection I would want to see you moving toward in making a decision as important as this one. When you can make the decision without shame and without defence--that is, on your terms and without hesitation--then you have likely done the work of getting to know yourself and your motivations better, and will likely be more happy with yourself, and ultimately, your choice.

Best to you and the choice you make.

What is Gender Nonconformity and how is it different from Gender Dysphoria?

This week’s column is from an anonymous question box at an American high school. All questions were submitted by students. If your school would like to install an anonymous question box for sexual health to be answered by The Pleasure Principal, please send an email.

Dear Pleasure Principal,

What is gender dysphoria?

Dear Teen,

Gender dysphoria is often confused with  Gender Nonconformity, and this is something that I hear even the experts at Planned Parenthood conflate, or mash together. Gender non-conformity  refers to people who do not follow other people's ideas or stereotypes about how they should look or act based on the female or male sex they were assigned at birth. Gender variance, or gender nonconformity, is behavior or gender expression by an individual that does not match masculine or feminine gender norms. For a delightfully useful article on gender terms and how they are used, check out this article in Vice, What's the difference between non-binary, genderqueer, and gender nonconforming?

It is extremely important to note that transgender individuals are at higher risk of victimization and hate crimes than the general public.

Gender dysphoria is the mental anguish that comes from being conflicted about one's assigned sex or how they identify in terms of sexual biology, assignment, and personal sexual expression. Researchers are uncertain whether the anguish and conflict is due to cognitive dissonance between identity and assignment or if it is due to the high levels of stigmatization, discrimination and victimization that occurs towards individuals who are outside of the gender binary. It would seem logical to believe it likely both. 

This stigmatisation and ostracisation frequently contributes to a negative self-image and increased rates of depression, anxiety, and other mental disorders.  Adolescents and adults with gender dysphoria are at increased risk for suicide.

In adolescents and adults, preoccupation with cross-gender issues can interfere with daily activities and cause problems in relationships or in functioning at school or work. Children with gender dysphoria may experience teasing and harassment at school or pressure to dress more like their assigned gender. Children with gender dysphoria are at higher risk of emotional and behavioral problems, including anxiety and depression.

Transgender individuals may also face challenges in accessing appropriate health care and insurance coverage of related services.

For more information on gender nonconformity:




If I date a girl who feels she is a guy, am I in a lesbian relationship?

This week’s column is from the mother of an 11-year-old. If you are a parent with a question about what your child is wondering or dealing with, email The Pleasure Principal.

Dear Pleasure Principal,

If I date a girl who feels she is a guy, am I in a lesbian relationship?

Dear Anonymous,

One of the things that is so interesting about how we categorise ourselves and our relationships is our need to categorise ourselves and our relationships. We are all, in the end, scientists of one kind or another. 

In this case, wanting to categorise sexual orientation based on sexual biology makes us social scientists. Even social scientists disagree on how we categorise sexuality, but it does generally describe five genders. It does not, however, have a definitive label on how to categorise people involved sexually with any of the non-conforming genders or non-binary people. 

That all said, dating is about getting to know another person. It is about developing trust, and we do that by learning about one another and sharing about ourselves. The more you are able to do that in relationship to anyone, the more you are going to have deeper intimacy and greater subjective well-being (personal satisfaction and contentment). It is far more important for you and the person you are dating to have open and frank communication about your true selves--your likes, dislikes, hopes, fears, aspirations, silliness, and maybe even some secrets. For some people, it is important to embrace the politics of dating outside of the gender binary, and this is covered extensively in Queer Studies in college. For some, it is a matter of safety to figure out how they are going to identify in relationship when talking to other important people in their life. It ultimately comes down to what you and the person you are developing deeper feelings for think about and agree on, both as individuals with strong core personal identities and as a couple. Does that make sense?